2105-96-6|4-Fluoro-3-nitrophenol| Ambeed

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Quality Control of [ 2105-96-6 ] Purity: 98% SDS Specification

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Product Details of [ 2105-96-6 ]

CAS No. :	2105-96-6
Formula :	C₆H₄FNO₃
M.W :	157.10
SMILES Code :	OC1=CC=C(F)C([N+]([O-])=O)=C1
MDL No. :	MFCD04038714
InChI Key :	JSRMPTJZAJUPGZ-UHFFFAOYSA-N
Pubchem ID :	16751861

Safety of [ 2105-96-6 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H315-H317-H318-H410
Precautionary Statements:	P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501
Class:	9
UN#:	3077
Packing Group:	Ⅲ

Computational Chemistry of [ 2105-96-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	37.25
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.79
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.4
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.86
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.7
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.35
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.88

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.03
Solubility	1.45 mg/ml ; 0.00925 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.39
Solubility	0.638 mg/ml ; 0.00406 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.47
Solubility	5.34 mg/ml ; 0.034 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.26 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.79

Application In Synthesis of [ 2105-96-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 2105-96-6 ]

[ 2105-96-6 ] Synthesis Path-Downstream 1~35

1
[ 42539-98-0 ]
[ 2105-96-6 ]

References: [1]Tetrahedron,1991,vol. 47,p. 705 - 714.

2
[ 2105-96-6 ]
[ 74-88-4 ]
[ 61324-93-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; at 40℃; for 6h;	4-Fluoro-3-nitrophenol (3.14 g) was dissolved in acetone (40 ml) . To the solution were added methyl iodide (5.68 g) and potassium carbonate (5.53 g) , and the mixture was stirred at 40°C for 6 hours. Then, methylene chloride (50 ml) was added thereto, the insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (50 ml) . The organic layer was washed with 1 N sodium hydroxide aqueous solution, water and brine, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give l-fluoro-4- methoxy-2 -nitrobenzene (3.47 g) as a brown oil.

References: [1]Chemical Communications,2003,p. 578 - 579.
[2]Patent: WO2012/169649,2012,A1 .Location in patent: Page/Page column 184; 185.

3
[ 2105-96-6 ]
[ 536-74-3 ]
C₁₄H₁₀N₄O₃ [ No CAS ]
[ 1680-44-0 ]

References: [1]Synlett,2007,p. 1591 - 1594.

4
[ 110-89-4 ]
[ 2105-96-6 ]
3-nitro-4-(piperidin-1-yl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
> 99%	With sodium hydrogencarbonate; In acetonitrile; at 70℃; for 13h;	A CH3CN (50 mL) solution of <strong>[2105-96-6]4-<strong>[2105-96-6]fluoro-3-nitrophenol</strong></strong> (4.71 g, 30 mmol), NaHCO3 (2.65 g, 31.5 mmol) and piperidine (3.02 mL, 30.6 mmol) was stirred at 70° C. for 13 days until less than 2percent starting material was left unreacted. Volatiles were removed in vacuo and the product was purified by silica gel column chromatography. Compound 3-nitro-4-(piperidin-1-yl)phenol was obtained as a reddish-brown color oil: 6.6 g (>99percent yield); 1H NMR (300 MHz, Chloroform-d) delta 7.23 (d, J=3.0 Hz, 1H), 7.10 (d, J=8.8 Hz, 1H), 6.98 (dd, J=8.8, 3.0 Hz, 1H), 5.14 (br s, 1H), 2.92-2.88 (m, 4H), 1.73-1.64 (m, 4H), 1.58-1.52 (m, 2H); LRMS (M+H) m/z 223.41.

References: [1]Patent: US2019/2455,2019,A1 .Location in patent: Paragraph 0669; 0670.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6070 - 6074.

5
[ 2105-96-6 ]
[ 16098-16-1 ]

References: [1]Chemical Communications,2003,p. 578 - 579.

6
[ 106-51-4 ]
[ 2105-96-6 ]

References: [1]Tetrahedron,1991,vol. 47,p. 705 - 714.

7
[ 400-93-1 ]
[ 403-42-9 ]
[ 2105-96-6 ]

Yield	Reaction Conditions	Operation in experiment
	With peracetic acid; sulfuric acid; nitric acid; acetic acid; In water;	Example 23 Preparation of 4-fluoro-3-nitrophenol (23) To 15 mL of concentrated sulfuric acid at 0° C. is added 6.9 g (0.05 mmol) of 4-fluoroacetophenone. To the resulting solution is rapidly added a mixture of 4 mL nitric acid and 6 mL concentrated sulfuric acid. The reaction mixture is stirred at 0-5° C. for 3 hours. The reaction mixture is then poured into ice water, and the resulting mixture is extracted with chloroform. The combined organic fractions are washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified using column chromatography on silica gel, eluding with 20percent ethyl acetate/hexanes, yielding 6.0 g of 4-fluoro-3-nitroacetophenone (60percent yield). Concentrated sulfuric acid (200 mL) and acetic acid (120) mL are mixed at 0° C. To this solution is added 15 g (0.082 mol) of 4-fluoro-3-nitroacetophenone with stirring. To the cold reaction mixture is added 36 mL of 36percent peracetic acid. The reaction mixture is then stirred at room temperature for 4 hours. Water (500 mL) is added to the mixture, and the crude product is extracted into diethyl ether. The combined ether fractions are washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified using column chromatography on silica gel, eluding with 3percent methanol/chloroform, giving 3.2 g of Compound 23 (20percent yield). mp: 86-87° C. 1 H-NMR (CDCl3) 7.56 (dd, 1H); 7.29 (t, 1H), 7.12 (m, 1H); 5.36 (s, 1H). 19 F-NMR (d6 -DMSO) 147.60 (s). Anal. calc. for C6 H4 FNO3: C, 45.87; H, 2.57; N, 8.92. Found: C, 45.80; H. 2.51; N, 8.69.

References: [1]Patent: US6162931,2000,A .

8
[ 2105-96-6 ]
[ 62257-16-3 ]

Yield	Reaction Conditions	Operation in experiment
39%	With iron; ammonium chloride; In ethanol; water; at 80℃; for 4h;	3-Amino-4-fluorophenol 4-Fluoro-3-nitrophenol (300 mg, 1.91 mmol) was initially charged in water (12.5 ml) and ethanol (12.5 ml). Ammonium chloride (552 mg, 10.31 mmol) and iron filings (640 mg, 11.46 mmol) were added and the mixture was stirred at 80° C. for 4 h. The reaction mixture was then cooled to RT and filtered through kieselguhr, and the filtrate was extracted with ethyl acetate. The organic phase was dried, filtered and concentrated. 126 mg (39percent of theory) of the title compound were obtained. LC/MS (Method 6, ESIpos): Rt=0.99 min, m/z=128 [M+H]+.
2.18 g (100%)	With H2;palladium on charcoal; In ethyl acetate;	Example 24 Preparation of 3-amino-4-fluorophenol (24) A mixture of <strong>[2105-96-6]4-<strong>[2105-96-6]fluoro-3-nitrophenol</strong></strong> (2.70 g, 17.2 mmol) and palladium on charcoal (10percent, 0.31 g) in 60 mL ethyl acetate is hydrogenated under 50 psi of H2 using a Parr hydrogenation reactor. After shaking for 1 hour, the reaction mixture is filtered using a diatomaceous earth pad to remove catalyst. The filtrate is concentrated in vacuo, and the residue is sublimed to yield 2.18 g (100percent) of Compound 24 as a white solid. MP: 142-144° C. 1 H-NMR (d6 -DMSO) 8.82 (s, 1H); 6.70 (dd, 1H); 6.17 (dd, 1H); 5.85 (m, 1H); 4.92 (s, 2H). 19 F-NMR (d6 -DMSO) 142.78 (t, 13.0 Hz). Anal. calc. for C6 H6 FNO: C, 56.69; H, 4.76; N, 11.02. Found: C, 57.28; H, 4.86; N, 10.65.

References: [1]Patent: US2017/253602,2017,A1 .Location in patent: Paragraph 0550-0552.
[2]Patent: US6162931,2000,A .

9
[ 120484-49-3 ]
[ 2105-96-6 ]
[ 935288-08-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 2h;	Reference Example 21; 2-Fluoro-5-[1-(2-fluoro-6-methoxyphenyl)ethoxy]aniline; To a solution of <strong>[2105-96-6]4-<strong>[2105-96-6]fluoro-3-nitrophenol</strong></strong> (this compound was synthesized according to the procedure described in the International publication WO97/39064) (0.2 g), 1-(2-fluoro-6-methoxyphenyl)ethanol (0.22 g) and triphenylphosphine (0.4 g) in tetrahydrofuran (1.5 mL) was added diisopropyl azodicarboxylate (40percent toluene solution, 0.84 mL) at room temperature, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane - n-hexane/ethyl acetate = 8/1) to give 2-fluoro-5-[1-(2-fluoro-6-methoxyphenyl)ethoxy]-1-nitrobenzene (0.15 g). This material was dissolved in tetrahydrofuran (3 mL). To the solution were added methanol (3 mL), nickel (II) bromide (5 mg) and sodium borohydride (55 mg) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. Then the mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 3/1) to give the title compound (0.11 g).

References: [1]Patent: EP1939204,2008,A1 .Location in patent: Page/Page column 17.

10
[ 2516-34-9 ]
[ 2105-96-6 ]
[ 1190631-52-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5191 - 5194.

11
[ 2105-96-6 ]
[ 75-03-6 ]
[ 10298-81-4 ]

Yield	Reaction Conditions	Operation in experiment
93%		To a DMF (10 mL) solution of <strong>[2105-96-6]4-fluoro-3-nitro-phenol</strong> (628 mg), sodium hydride (purity: 55percent or higher, 209 mg) was added in small portions at room temperature. After 30 minutes, ethyl iodide (0.38 mL) was added thereto at room temperature. After 2 hours, the reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate and saturated brine, then dried over sodium sulfate, and then concentrated. The residue was purified by column chromatography (hexane/ethyl acetate) to obtain the title compound (685 mg, 93percent) as a yellow solid. 1H NMR (400 MHz, CDCl3): delta (ppm) = 7.52 (1H, dd, J = 5.9 and 3.1 Hz), 7.23-7.13 (2H, m), 4.07 (2H, q, J = 7.0 Hz), 1.45 (3H, t, J = 7.0 Hz).

References: [1]Patent: EP2256105,2010,A1 .Location in patent: Page/Page column 67.

12
[ 64-67-5 ]
[ 2105-96-6 ]
[ 10298-81-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In acetonitrile; at 120℃; for 0.166667h;Microwave irradiation; Sealed vial;	To a stirred mixture of <strong>[2105-96-6]4-<strong>[2105-96-6]fluoro-3-nitrophenol</strong></strong> (200 mg, 1.27 mmol), potassium carbonate (185 mg, 1.34 mmol, OEt 1.05 equiv) and 2 mL MeCN in a 5 mL Pyrex microwave vial, diethyl sulfate (175 muL, 1.34 mmol, 1.05 equiv) was added. The suspension was stirred for 10 s and sealed with an aluminum crimp and Teflon septum. The reaction mixture was subjected to microwave heating for 10 min (hold time) at 120 °C and then cooled to 50 °C. The so processed reaction mixture was extracted with 2 .x. 25 mL EtOAc, the collected organic layers were dried over MgSO4, the solvent was removed under reduced pressure and the residue purified by flash chromatography (eluent - n-hexane/EtOAc; gradient 0 to 40percent AcOEt) to afford ethyl 4-ethoxy-1-fluoro-2-nitrobenzene (6a) as a white solid (233 mg, 99percent): m.p. = 63- 65 °C (2-propanol/H2O); 1H-NMR (300 MHz, CDCl3): d = 1.48 (t, J = 6.97 Hz, 3H), 4.09 (q,J = 7 Hz, 2H), 7.14-7.29 (m, 2H), 7.55 (dd, J = 5.8 and 2.9, 1H); GC-EIMS, m/z (percent): 157 (100), 185 (85).

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3731 - 3734.

13
[ 2105-96-6 ]
[ 1384512-54-2 ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3731 - 3734.

14
[ 2105-96-6 ]
2-(4-(2,5-difluorobenzyloxy)phenoxy)-5-ethoxyaniline [ No CAS ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3731 - 3734.

15
[ 2105-96-6 ]
3-amino-4-(4-methoxyphenylamino)phenol [ No CAS ]

References: [1]Patent: WO2013/123215,2013,A2 .

16
[ 2105-96-6 ]
1-(4-methoxyphenyl)-1H-benzo[d]imidazol-5-ol [ No CAS ]

References: [1]Patent: WO2013/123215,2013,A2 .

17
[ 2105-96-6 ]
[ 104-94-9 ]
4-(4-methoxyphenylamino)-3-nitrophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 165℃;	Synthesis of 4- (4-Methoxyphenylamino) -3-nitrophenol (compound 30?2)[0000170] To a solution of <strong>[2105-96-6]4-<strong>[2105-96-6]fluoro-3-nitrophenol</strong></strong> (2.0 g, 13 mmol, 1.0 equiv) in N-methyl-2-pyrrolidone (10 ml) was added N,N-diisopropylethylamine (2.2 mL, 13 mmol, 1.0 equiv) and 4- methoxyaniline (1.9 g, 15 mmol, 1.2 equiv) . The mixture was heated to 165 °C overnight, at which time LC-MS indicated that the reaction was complete. The mixture was cooled to room temperature and diluted with ethyl acetate. The organic phase was washed with water, saturated brine, dried over sodium sulfate and evaporated under reduced pressure. The compound was purified on an AnaLogix (SF 40-150 g) column using a gradient of 0-50percent ethyl acetate in heptanes over 45 minutes to give compound 30-2 as a red solid (2.2 g, 67percent yield)

References: [1]Patent: WO2013/123215,2013,A2 .Location in patent: Paragraph 0000170.

18
[ 2105-96-6 ]
N-((1-ethyl-1H-indazol-3-yl)methyl)-2-nitro-4-(quinolin-2-ylmethoxy)aniline [ No CAS ]